


The Guy With the Mark

by Notmenotthem



Category: Supernatural
Genre: Belts, Boots - Freeform, Kissing, Multi, Oral Sex, Pinching, Power Play, Spanking, Teasing, tied up, walking on you
Language: English
Status: Completed
Published: 2020-07-15
Updated: 2020-07-08
Packaged: 2021-03-04 02:34:28
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,964
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24836227
Author URL: https://archiveofourown.org/users/Notmenotthem/pseuds/Notmenotthem
Summary: You go out to check out a new club and on a bet, you and your friend pay "extra" to get a special service





	1. Chapter 1

You just HAD to come to this club, you just have to take that bet. Your friend was celebrating her breakup from her cheating boyfriend, and begged you to come out to party. You weren't alone, you had your friends with you. At the moment you just finished your shooter and was feeling buzzed. You told the bartender you just wanted a bottle of mineral water.

A hand slaps in front of you making you jump. Even in this loud nightclub, the sound makes you jump. 

"86' that water, she'll take a another shooter instead." 

What the fuck!? Who does this guy think he is? You turn to glare at him, when you look at his face your heart stops and the moisture in your mouth instantly dries up. He was staring at you with a cocky smile, with a hint of malice in his eyes. But when he stares at you, you immediately feel weak in the knees. The way he stares at you, you feel a tingling in your crouch. He must have noticed. He smirked at you. 

He pays for your drink and tips big to the bartender. 

"Thanks." You mouth. You were about to grab it, till he takes the drink out of your hand and downs it. 

'The hell!!?' He justs smirked. He gestured to the bartender and signals another for another one. When he brings it over he takes it and downs it again without breaking eye contact with you. Your mouth just hangs open as he displays such cocky behavior. When he orders another drink, this time a jello shot, he takes the drink and holds it in front of you. Then he did something SO outrageous, you were too shocked to react. He takes the drink and stuffs in your cleavage. Then he dips his head in it and sucks the drink up tilting his head back. You blink at him, then after he finished his drink he winks at you and walks away. 

You were just standing there in disbelief. What the hell just happened? You thoughts were interrupted when your bff comes over. 

"Hey! Y/N! Who's the hottie?" Your friend says. You just stare at him. You guys been friends forever, and he came with you to help let out from steam. 

"I don't know." You answer honestly. Your mind was still reeling on what just happened. Never had someone had displayed some cocky behavior. Usually you were the wallflower. The girl that is left behind to watch the purses while your friends dance with the men in the club, with you feeling jealous and sad you were basically just a equivalent of dried paint. But you couldn't help but think about the guy who literally put his head in your cleavage. The feelings of his face on you makes you blush. You look at your friend who was checking out the club. 

He was just dumped by Alicia. Dumb bitch found a newer, richer model and cruelly dumped your friend in the most humiliating way possible. She told everyone in your friend's shared Snapchat that she met her college sweetheart and was done with her current relationship. With a 💔👋. When you saw that you immediately went back to your own cruel breakup, when your ex sceamed that you were a "fucking idiot" for falling in love with him. And stole all your money leaving you crying in a dark alley at two am. 

"Whoever he is, he was checking you out all night." 

"Bullshit. I bet he and his friends made a bet to make fun of me. Won't be the first time." You mutter. Even as a adult, the feeling of being the recipient of the butt of jokes all through junior and high school never left you. Even when guys ask you out you were always suspicious of their motives. This will be no different. Feeling your eyes sting, your force yourself to blink hard. 

”Hey. Stop that! You are a working woman now. Those days are long gone. That guy was *definitely* checking you out. He was staring at your ass all night." 

The words sounded nice, but it felt wrong. 'Probably lost a bet, or felt sorry for me. Won't be the first time.' You give your friend a fake smile and excuse yourself. You head to the washroom and wait in line with the other girls. While waiting you overhear the ladies in front of you talking about a special "service." Apparently if you ask the bouncer in the VIP section anout the "Friday Night Special," you are possibly invited to an exclusive members only club. Unfortunately it won't guaranteed to get you in, no matter how attractive or rich you are. Being a famous celebrity? You will automatically be turned away. 

Hearing that, you couldn't help but feel intrigued. A exclusive members only club, only for the very elite. The girls in front of you continue to giggle and speculate what is behind those velvet ropes. When you glance at the VIP entrance, you see the cocky guy walk out. When he saw you looking at his direction, he winks at you. The girls in front of you immediately starts giggling. 

"Do you see that guy checking me out?" The blonde woman in front of you squeal. 

"Wrong, it was me he was looking at." Her friend with the leather pants say. 

When you look up, he was staring in your direction holding a beer in his hand. Not breaking eye contact, he takes a long, slow sip. The girls in front of you starts giggling, but you know deep down he was staring right at you. You could swear he was undressing you with his eyes. The club was cool, but you felt hot. Especially with your nipples starting to stick out. Dammit. 

Thankfully the line shortens, no thanks to the girls in front of you who decided to get out of the line and go to the VIP section to try to get in. You could couldn't help but smirk when the bouncer shakes his head. The hottie was gone. He went back inside. After you leave the washroom a few minutes later you go back to your friends. 

Your BFF gestures you over. "Y/N. I bought you a pop." 

"A pop? Why. I'm planning to get drunk tonight. Today is the night we celebrate our friend's new found freedom here." You gesture at your newly single friend. "Besides, it's the weekend." 

Geri shakes her head. "Nope. We have other plans. Y/N, you and BFF are going to the VIP section." 

"What! Why?" Your friend says. 

"The three of us here, not including you two, have to be somewhere. Besides, BFF, you were always complaining you played it safe. Same with Y/N here. You two, go to the VIP section and ask for the 'Friday Night Special.' C'mon, I dare you both. Besides, the sign says you need to be sober to get in." 

"And HOW do you know that?" BFF says. 

Liv smiles. "Because I was there last week. Geri here, was a regular last year. Same with Katie." 

Both of your jaws drop open. You always knew Liv was the wild one, but Geri and Katie were the 'safe' ones. Was Geri dumped because she was a regular 'customer?' Geri must have read your mind. She answered you. 

"Not just me, ex as well. Believe me, he came here more often than me. Rumors is there was a girl he fancied here. I didn't care. I had my own daddy." 

You guys just stare at each other. Katie speaks up. "Now it is your turn. Both of you, it is time to pop your cherry. Go to the back and ask for the 'special.' I promise, hell, we ALL promise you won't regret it." 

You and BFF stare at each other. BFF speaks up first. "Ha ha. Very funny. Who put you up to this? Was it Dave? Or was it my douchebag brother?" 

"No one. Okay. A friendly bet. Fifty bucks you will go to the back. If you stay here in the next five minutes, you both will owe us each fifty. If you guys get in, we each owe you fifty. How about it. An easy one hundred and fifty. How 'bout it. Y/N. I know you need cash for your rent." Liv says. 

"A hundred and fifty in free money? All we have to do is ask, and we get it? And if we get turned away, do we owe you?" BFF asks. You wonder the same thing. 

"All you have to do is ask." Katie says. They all pull out fifty's. This is yours tomorrow. Promise." 

"Deal." BFF shakes your friend's hands. Then he pulls you towards the VIP section. 

Your heart is beating fast. You were 99.9% sure you would be turned away. As for your friend, he'll get in. He is a man after all. 

"I want the Friday Night Special. Same with Y/N." He says. 

The bouncer nods and lets you in. When you see who is in the other side, your heart skips a beat. It was the cocky guy. Seeing you he smirks. When he sees your friend, he smiles at him as well. He waves you both in.


	2. The Room

**Summary for the Chapter:**

> This will be the female POV. With service from none other than Dean Winchester

He smirks at you both. "Okay. Who ordered the 'special.' Was it you, or the cleavage." He smirks at both of you. Even as he called you a sexist name, it didn't bother you at all. Your friend must have noticed, he was sweating as well. You couldn't help but stare at the mark on his arm. It was very unusual. He points at you first.

"K. The girl first. You," pointing at your friend, "Wait on the couch." He wiggles his finger at you in a 'come hither.' 

Obediently you wordlessly follow him. He takes your hand and slowly leads you to a darkened room. When you look around, there was others present. You weren't alone, there was couples everywhere in various states of undress. You couldn't help but feel nervous. You were no prude, but this was uncharted territory. He takes your hand and leads you to a private room. He takes you inside and stands in front of the door. Locking you inside. Feeling scared, you swallow hard.

He smirks at you. "I hope your swallowing skills are good. Just a question. You alright with that? I may be a demon, but I'm no rapist. Say the word, and I'll stop immediately." 

A demon? What kind of club is this? Oh. Legal reasons. He waits for your answer. You say 'Poughkeepsie.' Why? You have no idea. The word makes his eyebrows raise. He then nods at you. 

"See that swing there, go sit down. Do it!" He commands. You know when to obey. You sit on the swing.

He then walks towards and pushes you down. Then he lifts your legs in the air and proceeds to rub his hard on on your crotch. You couldn't help it. You moan loudly.

"Like that bitch? It gets better." He proceeds to lift up your top and rubs his surprisingly soft hands on your breasts. He squeezes them for a few seconds and then proceeds to play with your nipples. The feeling of his fingers makes you drip in arousal. You feel your underwear getting soaked. Him rubbing himself on you doesn't help you from moaning.

He smirks. He then gets off you with you groaning in disappointment. He then proceeds to take off his belt. Slowly. He makes a show of unbuckling his belt until it was off. He then drives you crazy when he puts it back on minute later.

"Can't see the merchandise yet, Princess. You have to work for it first. See my boots. Yeah, they cost me a small fortune. I had to rob several gas stations to buy them."

You stare at his feet. Those boots. You recognize them. Saint Laurent. Those boots cost more than your entire wardrobe. Lucky bastard. 

"I want you to go kiss them. Just one kiss on each boot." When he sees your disgusted expression. He smiles when he sees your face. "Then I want you to rub your face in my lap. Your whole face. Make it count. If you do it right, I'll reward you. Now be a good little girl." 

Your nervous as hell. But this guy is HOT. Your friends did say you play it safe too much. You nod. You bend down and plant a kiss on the left boot, then the next one. Then you proceed to slowlyyy rub your hands amoung his legs, which felt very muscular and firm. Mmm. You couldn't help but fantasize riding on top of those thighs bouncing on his cock. When you get to his crotch, you proceed to rub your face on him. You couldn't help but get turned on by his small moans.

His cock is hard against his jeans. You are tempted to unbuckle his belt and his jeans and blow him. But you don't. You want to earn his consent. Rubbing your face on his jeans, you feel your nipples getting hard. You also are very aware that you soaked through your jeans. Damn. He must have noticed. He orders you to sit up. 

He shakes his head. "Tsk. Tsk. You had ONE job. Bad girl. You know what happens to naughty girls, they get punished." He then proceeds to sit up and take off his belt. Folding the belt in half, he then proceeds to make scary noises with his belt. He makes a show of it. *Slap* The noise makes you jump. Maybe for many women the belt turns them on, but the sight of the belt brings up bad memories. 

"Poughkeepsie." Hearing that he stops. He then nods. 

"Okay then. A spanking. Take off your jeans and pull down your pants. But leave your panties on. Consider yourself lucky, I'm not touching your bare skin. Come bend over my lap and receive your punishment." 

You are nervous as hell. But you wonder what will happen next after your "punishment" is done. After you pull down your pants standing in nothing but your underwear, sans bra, since it is currently in the floor, you go over to the chair where he is sitting. He has his legs slightly spread open. When you drape yourself across his lap, he starts to spank you. 

*Smack.* "You bad girl. *Smack.* "How dare you disobey me. You didn't even greet me by my name.* The slaps on your ass hurt like a bitch, but you couldn't help but groan. 

You feel his fingers go to your pussy. He seems to be searching for your sweet spot. When he feels your clitoris, he rubs fingers over it. He doesn't do it very hard, he knows how sensitive it is. He knows exactly what he is doing. He couldn't help but moan when you rub yourself on his hard on with your chest. 

He plays with you for a few minutes more, until you cum. You couldn't help yourself. You let out a loud moan as you soak yourself on his hand. He smirks. 

"Baddd girl. Now I must punish you some more. Go lie down." Gesturing you to a mat on the floor he orders you to lay down. He the proceeds to take off his flannel shirt, and jeans. When you see him naked, your eyes go huge. He wasn't a 'giant' but he is even more beautiful nude. You want nothing more than to feel his whole body on you. 

Stupidly you blurt out, "I love you." Then immediately close your eyes in cringe. 'Whyyyy. Did. I. Say. That. God, I'm such a idiot.' You berate yourself. You don't dare open your eyes. You don't want him to pity you. 

"Your not the first one to tell me that. You won't be the last. Open your eyes. Now." 

When you open your eyes he then proceeds to sit on top of your chest. 

"Squeeze your tits together." When you squeeze your breasts together, he takes his cock and starts fucking your boobs. The sight of his cock head going towards your face, makes your tongue stick out. Your not sure if your allowed, but you hope to get a taste. He does. But it brushes on your tongue for a very *brief* frustratingly second. 

"No no no. Sorry. Not on the first night. This is only a taste. Enjoy it. That is all your gonna get. At least for now. Now keep squeezing your tits." 

He then fucks your boobs with you moaning. As much as you want him deep inside of you, the rules say you cannot be drunk. Drunk with lust, not booze. A few minutes later you hear him groan. Then you feel his cum all over your boobs and chest. Hearing that you scream out your own orgasm. 

When you come down from your high, you were shocked to see him bend down and kiss you. He kissed you for a few minutes then he pulled away. 

"Name's Dean. Consider yourself a member of 'Purgatory.' Next time you come in, just say your name, Y/N." 

How did he know your name? You didn't say your name. He smirks at you. 

"Can't be too greedy. Your friend is waiting. Have a good night. Princess. Next time, don't disobey me."


	3. Chapter 3

**Summary for the Chapter:**

> The male BFF will be known as Y/N in this story

You couldn't help but wonder what the hell is going on in this club. The music is loud and pulsating, but you couldn't help but hear your best friend screaming. As much as you want to go inside to see what is happening, you know that goes against the rules. You know she is usually the shy, quiet type, so whatever is happening to her, she is hopefully having a good time.

The door to the back opens and you are greeted at a sight. Your BFF face is bright red, and her very carefully applied hair and makeup is a disaster. Of course, you don't usually notice those things, but her whole look is unkempt. Plus her shirt is inside out. 

When she looks at you, ahe has a huge smile on her face. And when you give her a questioning look, ahe gave you a shaky smile. The guy that walked out behind her slapped her ass. And when she yelped, he grabbed her and gave her a huge dip kiss.

"Here. Get that ass on that couch. You." He points at you. "Your next. C'mon.'' He gestures you with a dirty look. Usually, that will make you want to punch him in the face, and grab your friend and leave, but your feet have a mind of their own. They ended up following him to what is behind that door..

Next thing you know you are standing in a room tied up to a weird contraption. Your hands and feet are secure tightly against the straps and you are almost naked, you are in your underwear. 

"What's going on?" You asked. 

"Shut it." The guy says. 

You wisely keep your mouth shut. Was this really a good idea? Yea, Alicia dumped you, and you agreed to go out with your childhood friend to cheer your friends up. But when they mentioned a secret club, both of you were curious. Then the sounds of a belt were coming off. Oh god. You dated women, but you made exceptions for special folk. Especially this guy. Damn. The last time you were with a man, you were in drunk and in college. But you had fun. He wasn't even a college student, but a guest professor. What was his name? Oh yeah, Chuck Shurley. 

"Ready for your punishment?" 

"I didn't do anything wrong!" 

"Consider this a early punishment then." 

*Slap!* *Snap!* 

Oh god the pain. But the more he hits you, the more you beg. Damn. That felt so good. *Snap!* Don't stop. Please! 

The more he hits you the more you beg. Alicia who? Who cares. If this guy wants me, fuck her. 

"Hmm. You are enjoying this way too much. I'm going to untie you then I want you to lie down on the floor." 

You feel blood coursing down your back. But painful as the whipping was, you don't mind it. Your back and legs *hurt* but whatever. You lay down your stomach, but he turns you around. Fuck. This guy is hot. He's wearing a flannel shirt with a pair of blue jeans. Other than that weird tattoo, which you have to admit looks nice, it was the boots that caught your eye. Ralph Lauren. Alicia before she dumped you bought you those for your birthday. You hadn't had a chance to wear them, the sight of them pains you. But on him, he looks like a sex god. Your sex god. 

He smirks at you. 

"Look at how pathetic you are. You are nothing but a bitch. You don't deserve to be comfortable. I want you naked. Take off those damn shorts. Now!" He commands. 

Doing what he asked, you wait for instructions. 

He doesn't say a word to you but proceeds to straddle you. His cock is hidden underneath his jeans, while yours is exposed. He then grinds you. Moaning and begging, he ignores your penis. Until he grabs your testicles and gives them a gentle squeeze. 

He doesn't say anything but when he gets up, he doea something odd. He walks on you. Step by step, he proceeded to walk on your naked body one booted foot at a time. He stops when he gets to your cock and balls. Then he proceeds to lift one foot up and plays with your cock with one foot. 

"Mmmnnn. Hmmh. You want me? Do you want this sweet dick? Or do you want to be fucked?" 

Oh my god. Did he just say what I think he said? Before you can answer, he sticks he foot in your mouth. 

"Give that boot a good blowjob. Maybe if you are nice, I'll give you a sample." 

You proceed to lick and suck that foot. His boot tastes awful, but what he offered will be worth it. After a few minutes he was done. Then he proceeds to unzip his jeans and pull out his cock. Holy shit. He then goes and sits on your chest and proceeds to jack himself off. 

"Hmmm. Mmmm. I want you to eat my cum. You can't taste me, not yet, but this will be your reward." 

It was pure torture seeing that penis. It was so close, but so far. That meaty sex smell makes you dizzy. His hands were so soft, especially the left one when he touches your face and opens up your mouth. 

"I'm cumming. Eat it bitch." 

A minute later his cock explodes cum all on your face and neck. He forcibly hold your mouth open while he cums. The taste of his cum is salty, but not unpleasant. Swallowing as much as you could, you were jerked off a minute later by him. He then proceeds to make you eat your own cum and his, by him scooping up what you made, and him wiping his cum off you in your mouth. The mix of both your cums makes you groan. 

"That is just a taste. Welcome to Purgatory. Name's Dean. Just ask for the 'special.' 

A few minutes later you and BFF are waiting for a cab. While you are waiting, your friend mentions a hot tall guy getting out of a ’67 Impala. Damn. Your friend has good taste. But you couldn't wait to have the Friday Night Special again.


End file.
